68066-85-3

Basic information

• Product Name: METHYL 1,2,3,4-TETRAHYDROQUINOLINE-4-CARBOXYLATE
• Synonyms: METHYL 1,2,3,4-TETRAHYDROQUINOLINE-4-CARBOXYLATE;1,2,3,4-Tetrahydroquinoline-4-carboxylic acid methyl ester;Methyl 1,2,3,4-tetrahydroxquinoline-4-carboxylate;1,2,3,4-Tetrahydro-4-quinolinecarboxylic acid methyl ester
• CAS NO: 68066-85-3
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.229
• Mol File: 68066-85-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 291.909 °C at 760 mmHg
• Flash Point: 130.342 °C
• Appearance: /
• Density: 1.125 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.03±0.40(Predicted)
• CAS DataBase Reference: METHYL 1,2,3,4-TETRAHYDROQUINOLINE-4-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 1,2,3,4-TETRAHYDROQUINOLINE-4-CARBOXYLATE(68066-85-3)
• EPA Substance Registry System: METHYL 1,2,3,4-TETRAHYDROQUINOLINE-4-CARBOXYLATE(68066-85-3)

Safety Data

• Hazardous Substances Data: 68066-85-3(Hazardous Substances Data)

Usage

General Description

Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate is an organic chemical compound. It is derived from quinoline, which is a heterocyclic aromatic organic compound, meaning it contains atoms of at least two different elements as part of its largest ring. Methyl 1,2,3,4-tetrahydroquinoline-4-carboxylate is typically used in research and development settings, such as synthesizing other chemicals in a laboratory. It's not typically used in everyday products or industrial applications. Its exact properties, including toxicity, environmental impact, and potential health effects, are not well documented or known, indicating it is a specialized chemical primarily for scientific research.

Upstream product

• 340269-83-2 2-(2-nitro-phenyl)-4-oxo-butyric acid methyl ester 
• 30095-98-8 methyl (2-nitrophenyl)acetate 
• 274676-13-0 methyl (+/-)-2-(2-nitrophenyl)-4-pentenoate 
• 21233-61-4 quinoline-4-carboxylic acid methyl ester 
• 486-74-8 4-quinolinic acid 

Downstream Products

• 1224639-56-8 1-[2-(2,5-dichloro-phenoxy)-5-fluoro-pyridine-3-carbonyl]-1,2,3,4-tetrahydro-quinoline-4-carboxylic acid methyl ester 

Relevant articles and documents

Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer

The direct reduction of arenes and heteroarenes by visible-light irradiation remains challenging, as the energy of a single photon is not sufficient for breaking aromatic stabilization. Shown herein is that the energy accumulation of two visible-light photons allows the dearomatization of arenes and heteroarenes. Mechanistic investigations confirm that the combination of energy-transfer and electron-transfer processes generates an arene radical anion, which is subsequently trapped by hydrogen-atom transfer and finally protonated to form the dearomatized product. The photoreduction converts planar aromatic feedstock compounds into molecular skeletons that are of use in organic synthesis.

Diastereoselective synthesis of substituted tetrahydroquinoline-4-carboxylic esters by a tandem reduction-reductive amination reaction

A diastereoselective synthesis of 1-methyl-2-alkyl- and 2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylic esters has been developed from methyl (2-nitrophenyl)acetate (1). The method involves alkylation of 1 with an allylic halide, ozonolysis of the double bond, and catalytic hydrogenation. The final hydrogenation initiates a tandem sequence involving (1) reduction of the aromatic nitro group, (2) condensation of the aniline or hydroxylamine8 nitrogen with the side chain carbonyl, (3) reduction of the resulting nitrogen intermediate, and (4) reductive amination of the tetrahydroquinoline with formaldehyde produced in the ozonolysis to give a methyl (±)-1-methyl-2-alkyl-1,2,3,4-tetrahydroquinoline-4-carboxylate. Removal of the formaldehyde prior to hydrogenation gives the simple (±)-2-alkyl derivatives. The products are isolated in high yield as single diastereomers having the C-2 alkyl group cis to the C-4 carboxylic ester. The reaction has been extended to the synthesis of tricyclic structures with similar high diastereoselection.